Chappelle's comment isn't accurate.

What Chappelle is referring to is the famous Oct. 16, 1901 dinner where he hosted Booker T. Washington at the White House. At the time, Washington was president of the Tuskegee Institute and the most influential black leader in the United States. As Washington later wrote in My Larger Education, "It was merely an incident that had no thought or motive behind it except the convenience of the President."

That dinner didn't have any precedent: No black man had ever been invited to dine with the president before, at least not as relative equals.

It wasn't a formal state dinner, just a quiet event; the only other people there were the president's wife, daughter, three sons and one of the president's friends.

It was only publicized with a two-line press release the following day, but the event kicked off a firestorm of protest across the South, with newspaper editorials condemning Roosevelt's action to various degrees. As the Tampa Morning Tribune wrote on Oct. 20: "Washington is, no doubt, a very respectable negro, the leader of his race, a man whose influence among his people is far their betterment and unlifting. But even an educated negro has his place, and it is not at the dining-table of the chief magistrate of the republic."

In a letter published in the Oct. 29 issue of the Jacksonville Metropolis newspaper, resident E.Y. Harvey wrote, "Not from Southerners nor Democrats alone do we hear the protest against the President's action, but it is the voice of the American people. Eating at the same table means social equality. Social equality means free right of inter-marriage, and inter-marriage means the degradation of the white race. When the white race yields social equality with the negro it has defied the laws of God, and he will sweep them from the earth."

Roosevelt had previously leaned on Washington as an adviser on racial issues. He needed Washington, he thought, to understand the Southern mindset and what black Americans wanted from a Republican president at a time when the black vote was universally for the Republican Party. In the 1904 election, Roosevelt knew he would have to have black support, and Washington was a way to get that support. Southern whites generally ignored Washington's status as an adviser because it was informal, wasn't generally known, and the scope of his influence wasn't clear. After all, during the 1900 election, Roosevelt had called himself "half a Southerner" because some of his family had served in the Confederate Army.

That perception changed with the dinner, but it didn't scare off Roosevelt, nor did it stop him from meeting with Washington again, nor did it stop him from meeting Washington in the White House.

In Dewey Grantham's 1958 paper Dinner at the White House: Theodore Roosevelt, Booker T. Washington, and the South (it might be old, but it's still cited frequently) Grantham quotes from Roosevelt's personal letters in the wake of the incident:

"At the same time, he was angered by the attacks against him and he let it be known privately that he would have Booker T. Washington 'to dine just as often as I please' ─ he would not be intimidated by 'the idiot or vicious Bourbon element of the South.' 'If these creatures had any sense they would understand that they can't bluff me,' the President wrote his friend Henry Cabot Lodge."

Roosevelt did continue to invite Washington to the White House, but he made sure to schedule the meetings for midmorning so as to not cross mealtimes.

Furthermore, Roosevelt continued to inflame the South on racial issues. Though he campaigned in the South with the fact that he had appointed fewer black Americans and more white Democrats to federal positions than any previous Republican President, some of his appointments caused a stir. In 1903, he appointed a black man named William Crum to be Collector of the Port of Charleston. Crum was a respected black leader, but segregationist Southern politicians blocked his confirmation again and again throughout Roosevelt's term in office. Again and again, Roosevelt foiled them by appointing Crum during the Congressional recess. When Roosevelt finally left office in 1909, Crum resigned having never been confirmed to office.

In 1901, Roosevelt caused a stir when he closed the post office in Indianola, Mississippi when the black postmistress there resigned from her office. Local whites wanted the post office to be reopened under a white postmaster, but Roosevelt refused ─ at least for a few years.

Roosevelt's racial record is at best an imperfect one, and at worst downright racist (especially by modern standards), but in this particular case, Chappelle isn't remembering the story accurately.

Edit: I should point out that Booker T. Washington died 101 years ago today.

Can I ask who was the first African American invited to the white house? I've tried to research the answer and it seems to be Frederick Douglas, but not positive. I asked in another thread but have not gotten a response.